organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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COMMUNICATIONS
ISSN: 2056-9890

N′-(4-Ethyl­cyclo­hexyl­­idene)-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Beyazit, Istanbul, Turkey, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 22 July 2013; accepted 23 July 2013; online 27 July 2013)

The title compound, C23H24FN3O, crystallizes with two independent mol­ecules (I and II) in the asymmetric unit. These pairs of mol­ecules are linked to each other as N—H⋯O dimers with an R22(10) motif. Furthermore, the crystal structure also exhibits C—H⋯π inter­actions. The atoms of the ethyl group in mol­ecule I are disordered over two sites with an occupancy ratio of 0.817 (6):0.183 (6).

Related literature

For the anti­tubercular and anti­viral activity of variously substituted N-(1-thia-4-aza­spiro­[4.5]dec-4-yl)carboxamides, see: Cihan-Üstündağ & Çapan (2012[Cihan-Üstündağ, G. & Çapan, G. (2012). Mol. Divers. 16, 525-539.]); Göktas et al. (2012[Göktas, F., Vanderlinden, E., Naesens, L., Cesur, N. & Cesur, Z. (2012). Bioorg. Med. Chem. 20, 7155-7159.]). For similar structures, see: Çelikesir et al. (2013a[Çelikesir, S. T., Akkurt, M., Üstündağ, G. C. & Büyükgüngör, O. (2013a). Acta Cryst. E69, o1202.],b[Çelikesir, S. T., Akkurt, M., Üstündağ, G. C., Çapan, G. & Büyükgüngör, O. (2013b). Acta Cryst. E69, o1211-o1212.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C23H24FN3O

  • Mr = 377.45

  • Triclinic, [P \overline 1]

  • a = 11.8121 (5) Å

  • b = 13.3802 (5) Å

  • c = 15.5693 (6) Å

  • α = 114.328 (3)°

  • β = 95.642 (3)°

  • γ = 110.434 (3)°

  • V = 2014.85 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.55 × 0.48 × 0.37 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.955, Tmax = 0.969

  • 30678 measured reflections

  • 8272 independent reflections

  • 5564 reflections with I > 2σ(I)

  • Rint = 0.108

Refinement
  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.180

  • S = 1.02

  • 8272 reflections

  • 528 parameters

  • 8 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg3, Cg5 and Cg7 are the centroids of the N1/C1/C6/C7/C14, C8–C13, N4/C24/C29/C30/C37 and C31–C36 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O2 0.85 (3) 2.00 (3) 2.836 (3) 168 (3)
N4—H4N⋯O1 0.85 (3) 2.08 (3) 2.887 (3) 160 (2)
C9—H9⋯Cg1i 0.93 2.81 3.636 (3) 149
C17—H17ACg3 0.97 2.87 3.820 (3) 165
C40—H40ACg7 0.97 2.79 3.727 (4) 163
C40—H40BCg5ii 0.97 2.65 3.595 (4) 163
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+2.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

On reaction with mercaptoalkanoic acids, cyclohexylidenehydrazides smoothly afford N-(1-thia-3-oxo-4-azaspiro[4.5]dec-4-yl)carboxamides with promising antituberculosis (Cihan-Üstündağ & Çapan, 2012) and antiviral (Göktas et al., 2012) activity. We have recently reported on the crystal structures of two such precursors (Türktekin-Çelikesir et al., 2013a,b). We herein report the X-ray diffraction analysis of the title compound.

In the title compound, (Fig. 1), the asymmetric unit contains two crystallographically independently molecules whose cyclohexane rings adopt chair conformations [the puckering parameters (Cremer & Pople, 1975) are QT = 0.507 (4) Å, θ = 4.0 (6)°, ϕ = 277 (7)° for molecule I (with N1), and QT = 0.531 (4) Å, θ = 12.5 (4) °, ϕ = 205.2 (18) ° for molecule II (with N4)].

The indole ring systems of both molecules I and II are essentially planar [maximum deviations are 0.026 (4) Å for C3 in molecule I and 0.028 (2) Å for C30 in molecule II]. The indole ring systems of molecules I and II make dihedral angles of 77.93 (12) and 77.66 (14)° with their phenyl rings, respectively.

In the crystal, pairs of molecules I and II in the asymmetric unit are linked to each other, forming N—H···O dimers (Table 1, Fig. 2), with the R22(10) ring motif (Bernstein et al., 1995). In addition, C—H···π interactions (Table 1) contribute to the stabilization of the crystal structure.

Related literature top

For the antitubercular and antiviral activity of variously substituted N-(1-thia-4-azaspiro[4.5]dec-4-yl)carboxamides, see: Cihan-Üstündağ & Çapan (2012); Göktas et al. (2012). For similar structures, see: Çelikesir et al. (2013a,b). For puckering analysis, see: Cremer & Pople (1975). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

A mixture of 5-fluoro-3-phenyl-1H-indole-2-carbohydrazide (0.005 mol) and 4-ethyl cyclohexanone (0.007 mol) was refluxed in 15 ml absolute ethanol for 5 h. The precipitate obtained on cooling was purified by recrystallization from an ethanol-water mixture to afford colorless prisms.

[Yield: 79%, m.p.: 451.0- 452.5 K]. IR(KBr): υmax 3346, 3235 (N—H), 1654 (C=O) cm-1. 1H-NMR (DMSO-d6/500 MHz): δ 0.84 (t, 3H, J= 7.2 Hz, 4-CH2CH3-cyc.*), 1.13 (br. d, 1H,J=6.8 Hz, CH/CH2-cyc.), 1.19 (br. t, 2H, J=6.6 Hz, 4-CH2CH3-cyc.), 1.33 (s, 1H, CH/ CH2-cyc.), 1.48 (br. s, 1H, CH/CH2-cyc.), 1.61 (d, 2H, J=12.7 Hz, CH/CH2-cyc.), 1.70–1.90 (m, 2H, CH/CH2-cyc.), 2.13 (s, 1H, CH/CH2-cyc.), 2.30 (s, 1H, CH/CH2-cyc.), 7.12 (br. t, 2H, J= 8.8 Hz, H4, H6-ind.), 7.42–7.51 (m, 6H, H7, 3-C6H5-ind.), 9.44 (s, 1H, CONH), 12.03 (s, 1H, NH) p.p.m.. 13C-NMR(APT, DMSO-d6/125 MHz): δ 12.12 (4-CH2CH3-cyc.), 26.06 (CH2-cyc.), 28.79 (4-CH2CH3-cyc.), 31.88 (CH2-cyc.), 32.86 (CH2-cyc.), 34.65 (CH2-cyc.), 38.32 (CH-cyc.), 104.64 (d, J=23.5 Hz, C4-ind.), 113.50 (d, C6-ind.), 114.40 (C7-ind.), 118.00 (C3-ind.), 126.80 (C3a-ind.), 128.54 (3-C6H5 (C4)-ind.), 129.68 (3-C6H5(C3,C5)-ind.), 129.91 (C2-ind.), 130.90 (3-C6H5(C2,C6)-ind.), 133.03** (C7a-ind.), 134.02** (3-C6H5(C1)-ind.), 158.24 (C=N), 158.30 (d, J=233.6 Hz, C5-ind.), 162.11 (C=O) p.p.m.. MS (APCI+) m/z (%) 378 ((M+H)+, 100), (APCI–) m/z (%) 376 ((M—H)-, 100). Analysis calculated for C23H24FN3O: C 73.19, H 6.41, N 11.13%. Found: C 72.84, H 6.68, N 10.93%.(*cyc.=cyclohexylidene, br.=broad, ind.=indole, **interchangeable).

Refinement top

H atoms bonded to C atoms were positioned geometrically with C—H = 0.93 - 0.98 Å, and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C). The H atoms of the four amide groups were found in a difference Fourier map, and refined freely. The atoms of the ethyl group in molecule I (with N1) are disordered over two sites (with the suffixes A and B) with the refined occupancy ratio of 0.817 (6):0.183 (6). The atoms of the disordered ethyl group in molecule I were set to equal each other by an EADP instruction. Four poorly fitted reflections (1 - 3 1), (2 - 1 2), (1 - 3 3) and (3 - 2 1) were omitted from the refinemet.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the pairs of molecules I and II of the title compound in the asymmetric unit. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. View of the N—H···O dimer between the pairs of molecules I and II in the asymmetric unit. H atoms not participating in hydrogen bonding have been omitted for clarity.
N'-(4-Ethylcyclohexylidene)-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide top
Crystal data top
C23H24FN3OZ = 4
Mr = 377.45F(000) = 800
Triclinic, P1Dx = 1.244 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.8121 (5) ÅCell parameters from 34554 reflections
b = 13.3802 (5) Åθ = 2.0–27.3°
c = 15.5693 (6) ŵ = 0.08 mm1
α = 114.328 (3)°T = 296 K
β = 95.642 (3)°Prism, colourless
γ = 110.434 (3)°0.55 × 0.48 × 0.37 mm
V = 2014.85 (17) Å3
Data collection top
Stoe IPDS 2
diffractometer
8272 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus5564 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.108
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 2.3°
ω–scansh = 1414
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1616
Tmin = 0.955, Tmax = 0.969l = 1919
30678 measured reflections
Refinement top
Refinement on F28 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.067 W = 1/[Σ2(FO2) + (0.083P)2 + 0.3779P] WHERE P = (FO2 + 2FC2)/3
wR(F2) = 0.180(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.35 e Å3
8272 reflectionsΔρmin = 0.19 e Å3
528 parameters
Crystal data top
C23H24FN3Oγ = 110.434 (3)°
Mr = 377.45V = 2014.85 (17) Å3
Triclinic, P1Z = 4
a = 11.8121 (5) ÅMo Kα radiation
b = 13.3802 (5) ŵ = 0.08 mm1
c = 15.5693 (6) ÅT = 296 K
α = 114.328 (3)°0.55 × 0.48 × 0.37 mm
β = 95.642 (3)°
Data collection top
Stoe IPDS 2
diffractometer
8272 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
5564 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.969Rint = 0.108
30678 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0678 restraints
wR(F2) = 0.180H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.35 e Å3
8272 reflectionsΔρmin = 0.19 e Å3
528 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F10.05143 (16)0.22445 (17)0.21734 (13)0.0940 (6)
O10.59795 (19)0.40150 (17)0.65907 (12)0.0752 (7)
N10.3715 (2)0.2028 (2)0.53565 (15)0.0612 (7)
N20.7073 (2)0.3010 (2)0.58120 (15)0.0662 (8)
N30.8220 (2)0.3863 (2)0.65017 (14)0.0699 (8)
C10.2761 (2)0.0988 (2)0.46077 (16)0.0578 (8)
C20.1458 (3)0.0503 (3)0.4466 (2)0.0717 (10)
C30.0724 (3)0.0574 (3)0.3636 (2)0.0743 (10)
C40.1284 (3)0.1150 (3)0.29687 (19)0.0686 (9)
C50.2541 (2)0.0691 (2)0.30711 (17)0.0623 (8)
C60.3310 (2)0.0409 (2)0.39164 (16)0.0542 (8)
C70.4643 (2)0.1138 (2)0.42771 (15)0.0524 (7)
C80.5555 (2)0.0856 (2)0.37421 (15)0.0521 (7)
C90.5933 (3)0.0018 (2)0.3731 (2)0.0710 (10)
C100.6731 (3)0.0321 (3)0.3197 (2)0.0847 (11)
C110.7165 (3)0.0241 (3)0.2664 (2)0.0914 (12)
C120.6810 (3)0.1118 (4)0.2665 (2)0.0949 (14)
C130.6016 (3)0.1429 (3)0.3202 (2)0.0717 (10)
C140.4853 (2)0.2117 (2)0.51692 (16)0.0547 (8)
C150.6011 (2)0.3143 (2)0.59215 (16)0.0577 (8)
C160.9194 (3)0.3713 (3)0.63047 (18)0.0691 (9)
C170.9279 (3)0.2770 (3)0.5408 (2)0.0833 (11)
C181.0327 (4)0.3371 (4)0.5030 (3)0.1061 (18)
C191.1560 (3)0.4280 (4)0.5781 (3)0.1004 (16)
C201.1385 (3)0.5181 (4)0.6656 (3)0.1005 (16)
C211.0427 (3)0.4600 (3)0.7075 (2)0.0902 (11)
C22A1.2593 (5)0.4974 (5)0.5436 (4)0.110 (2)0.817 (6)
C23A1.3041 (6)0.4198 (6)0.4711 (5)0.126 (3)0.817 (6)
C23B1.366 (2)0.508 (2)0.537 (2)0.126 (3)0.183 (6)
C22B1.2352 (13)0.4138 (18)0.5038 (15)0.110 (2)0.183 (6)
F20.6710 (2)1.04361 (17)0.94884 (19)0.1217 (9)
O20.31889 (19)0.31546 (16)0.71583 (12)0.0730 (6)
N40.4818 (2)0.5522 (2)0.76600 (14)0.0581 (7)
N50.2973 (2)0.37572 (19)0.86894 (15)0.0569 (7)
N60.21921 (19)0.26057 (17)0.85033 (14)0.0580 (7)
C240.5392 (2)0.6749 (2)0.80253 (17)0.0586 (8)
C250.6219 (3)0.7449 (3)0.7690 (2)0.0719 (10)
C260.6642 (3)0.8682 (3)0.8203 (2)0.0820 (11)
C270.6270 (3)0.9203 (3)0.9024 (3)0.0831 (11)
C280.5475 (3)0.8556 (3)0.9381 (2)0.0725 (10)
C290.5031 (2)0.7290 (2)0.88695 (17)0.0569 (8)
C300.4220 (2)0.6328 (2)0.90166 (15)0.0529 (7)
C310.3655 (2)0.6474 (2)0.98483 (15)0.0526 (7)
C320.4393 (3)0.6817 (3)1.07581 (18)0.0729 (10)
C330.3872 (3)0.6855 (3)1.15265 (19)0.0841 (10)
C340.2624 (3)0.6584 (3)1.1401 (2)0.0803 (10)
C350.1891 (3)0.6286 (3)1.0519 (2)0.0867 (11)
C360.2405 (3)0.6232 (3)0.97499 (19)0.0749 (10)
C370.4113 (2)0.5258 (2)0.82567 (15)0.0521 (7)
C380.3391 (2)0.3971 (2)0.79784 (15)0.0528 (8)
C390.1917 (2)0.2488 (2)0.92415 (17)0.0579 (8)
C400.2397 (3)0.3436 (3)1.03009 (18)0.0736 (10)
C410.1395 (3)0.3362 (3)1.0833 (2)0.0788 (10)
C420.0615 (3)0.2083 (3)1.0657 (2)0.0745 (10)
C430.0033 (3)0.1244 (3)0.9559 (2)0.0751 (10)
C440.1045 (3)0.1235 (2)0.9033 (2)0.0770 (10)
C450.0340 (3)0.2019 (3)1.1234 (2)0.0901 (12)
C460.0227 (4)0.2544 (4)1.2315 (3)0.1145 (16)
H20.110200.089900.492200.0860*
H1N0.362 (2)0.246 (2)0.5898 (19)0.062 (7)*
H50.287700.109200.260000.0750*
H90.564100.040900.409300.0850*
H100.697400.091000.320000.1020*
H110.770200.003400.229900.1090*
H120.710900.150300.230000.1130*
H2N0.693 (2)0.237 (3)0.534 (2)0.072 (8)*
H30.014700.092000.351600.0890*
H17B0.945900.219800.556000.1000*
H18A1.046700.273700.452400.1270*
H18B1.002900.376800.472300.1270*
H191.189500.383100.601000.1200*
H20A1.112400.569300.647100.1200*
H20B1.218600.569700.716100.1200*
H21A1.074100.418300.734900.1080*
H21B1.030000.522500.760200.1080*
H22A1.226500.537500.515100.1310*0.817 (6)
H22B1.330400.559900.600400.1310*0.817 (6)
H23A1.368600.468800.453700.1900*0.817 (6)
H23B1.235100.359600.413400.1900*0.817 (6)
H23C1.337700.380500.498800.1900*0.817 (6)
H130.578600.202700.320200.0860*
H17A0.848000.232700.490200.1000*
H22C1.238400.336100.483200.1310*0.183 (6)
H22D1.190200.410200.446200.1310*0.183 (6)
H23D1.393500.507100.480300.1900*0.183 (6)
H23E1.420600.492000.573800.1900*0.183 (6)
H23F1.369400.586600.577100.1900*0.183 (6)
H4N0.498 (2)0.498 (2)0.7245 (19)0.065 (7)*
H5N0.314 (2)0.436 (2)0.9156 (14)0.051 (7)*
H250.647000.708800.713900.0860*
H260.718300.917400.799600.0990*
H280.524200.893800.993600.0870*
H320.525100.702501.085600.0870*
H330.437700.706701.212800.1010*
H340.227200.660001.191300.0960*
H350.104300.611901.043600.1040*
H360.189500.602900.915400.0900*
H40A0.274800.423301.034300.0880*
H40B0.307200.335001.062800.0880*
H41A0.083800.365501.062100.0940*
H41B0.179400.389201.153300.0940*
H420.120100.181301.088100.0890*
H43A0.047300.042600.943800.0900*
H43B0.051600.151300.930100.0900*
H44A0.153100.087700.923700.0920*
H44B0.064900.073300.833000.0920*
H45A0.081100.245001.114000.1080*
H45B0.093000.117601.097300.1080*
H46A0.080400.338201.258300.1370*
H46B0.066900.210301.241700.1370*
H46C0.042900.248201.263500.1370*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0663 (10)0.0881 (12)0.0889 (11)0.0211 (9)0.0103 (8)0.0211 (9)
O10.0809 (13)0.0725 (11)0.0617 (10)0.0379 (10)0.0299 (9)0.0169 (9)
N10.0721 (14)0.0673 (13)0.0537 (11)0.0388 (12)0.0331 (10)0.0267 (10)
N20.0667 (14)0.0652 (14)0.0505 (11)0.0296 (12)0.0162 (10)0.0125 (10)
N30.0718 (15)0.0743 (14)0.0499 (10)0.0305 (12)0.0137 (10)0.0194 (10)
C10.0628 (15)0.0659 (15)0.0558 (12)0.0330 (13)0.0259 (11)0.0323 (11)
C20.0692 (18)0.092 (2)0.0718 (16)0.0448 (16)0.0382 (14)0.0425 (15)
C30.0604 (17)0.089 (2)0.0780 (17)0.0322 (16)0.0249 (14)0.0426 (16)
C40.0621 (17)0.0685 (16)0.0665 (15)0.0248 (14)0.0164 (12)0.0279 (13)
C50.0657 (16)0.0654 (15)0.0575 (13)0.0318 (13)0.0246 (11)0.0264 (12)
C60.0584 (14)0.0615 (14)0.0534 (12)0.0316 (12)0.0239 (10)0.0302 (11)
C70.0598 (14)0.0562 (13)0.0493 (11)0.0292 (12)0.0238 (10)0.0271 (10)
C80.0539 (13)0.0541 (13)0.0461 (10)0.0241 (11)0.0194 (9)0.0203 (9)
C90.089 (2)0.0674 (16)0.0799 (16)0.0468 (16)0.0427 (15)0.0405 (14)
C100.091 (2)0.0739 (19)0.100 (2)0.0515 (18)0.0443 (18)0.0340 (17)
C110.084 (2)0.101 (2)0.087 (2)0.050 (2)0.0496 (17)0.0290 (18)
C120.099 (2)0.128 (3)0.093 (2)0.059 (2)0.0607 (19)0.068 (2)
C130.0769 (18)0.0859 (19)0.0782 (16)0.0440 (16)0.0393 (14)0.0506 (15)
C140.0636 (15)0.0586 (13)0.0517 (11)0.0326 (12)0.0276 (10)0.0273 (10)
C150.0711 (16)0.0626 (14)0.0490 (11)0.0346 (13)0.0290 (11)0.0277 (11)
C160.0723 (18)0.0768 (17)0.0557 (13)0.0328 (15)0.0174 (12)0.0290 (12)
C170.079 (2)0.089 (2)0.0744 (17)0.0402 (18)0.0249 (15)0.0286 (16)
C180.107 (3)0.155 (4)0.082 (2)0.077 (3)0.041 (2)0.059 (2)
C190.080 (2)0.133 (3)0.129 (3)0.049 (2)0.037 (2)0.094 (3)
C200.077 (2)0.105 (3)0.113 (3)0.036 (2)0.0085 (19)0.053 (2)
C210.071 (2)0.104 (2)0.0746 (18)0.0330 (18)0.0043 (15)0.0319 (17)
C22A0.110 (4)0.102 (4)0.141 (4)0.048 (3)0.050 (3)0.074 (4)
C23A0.134 (5)0.165 (6)0.138 (5)0.078 (5)0.078 (4)0.103 (4)
C23B0.134 (5)0.165 (6)0.138 (5)0.078 (5)0.078 (4)0.103 (4)
C22B0.110 (4)0.102 (4)0.141 (4)0.048 (3)0.050 (3)0.074 (4)
F20.1159 (17)0.0648 (11)0.170 (2)0.0284 (12)0.0460 (15)0.0509 (12)
O20.0988 (14)0.0617 (10)0.0562 (9)0.0350 (10)0.0394 (9)0.0219 (8)
N40.0674 (13)0.0624 (13)0.0530 (10)0.0330 (11)0.0272 (9)0.0285 (10)
N50.0665 (13)0.0514 (12)0.0492 (10)0.0246 (11)0.0224 (9)0.0203 (9)
N60.0610 (12)0.0545 (11)0.0594 (11)0.0257 (10)0.0260 (9)0.0255 (9)
C240.0588 (14)0.0657 (15)0.0608 (13)0.0304 (13)0.0192 (11)0.0352 (12)
C250.0691 (17)0.087 (2)0.0766 (16)0.0347 (16)0.0277 (13)0.0516 (15)
C260.0702 (19)0.081 (2)0.107 (2)0.0257 (17)0.0264 (16)0.0609 (18)
C270.0718 (19)0.0621 (17)0.113 (2)0.0248 (15)0.0224 (17)0.0439 (17)
C280.0696 (17)0.0651 (16)0.0833 (17)0.0340 (15)0.0228 (14)0.0316 (14)
C290.0574 (14)0.0590 (14)0.0613 (13)0.0304 (12)0.0184 (11)0.0300 (11)
C300.0543 (13)0.0567 (13)0.0512 (11)0.0288 (11)0.0167 (10)0.0244 (10)
C310.0575 (14)0.0513 (12)0.0472 (11)0.0281 (11)0.0171 (10)0.0176 (9)
C320.0635 (17)0.091 (2)0.0556 (13)0.0333 (15)0.0156 (12)0.0278 (13)
C330.096 (2)0.099 (2)0.0509 (13)0.0426 (19)0.0214 (14)0.0296 (14)
C340.099 (2)0.0750 (18)0.0646 (16)0.0385 (17)0.0440 (16)0.0260 (14)
C350.0663 (18)0.108 (2)0.0825 (19)0.0433 (18)0.0366 (15)0.0345 (17)
C360.0630 (16)0.101 (2)0.0584 (14)0.0444 (16)0.0183 (12)0.0284 (14)
C370.0587 (14)0.0600 (13)0.0476 (11)0.0311 (12)0.0219 (10)0.0284 (10)
C380.0591 (14)0.0622 (14)0.0477 (11)0.0351 (12)0.0238 (10)0.0261 (10)
C390.0583 (14)0.0600 (14)0.0642 (13)0.0306 (12)0.0244 (11)0.0315 (11)
C400.0717 (18)0.0780 (18)0.0615 (14)0.0174 (15)0.0172 (13)0.0375 (14)
C410.090 (2)0.0697 (17)0.0641 (15)0.0232 (16)0.0301 (14)0.0285 (13)
C420.0787 (19)0.0749 (18)0.0763 (17)0.0306 (15)0.0328 (14)0.0414 (14)
C430.0750 (19)0.0592 (15)0.0782 (17)0.0153 (14)0.0270 (14)0.0317 (13)
C440.089 (2)0.0598 (16)0.0830 (18)0.0299 (15)0.0360 (15)0.0340 (14)
C450.095 (2)0.088 (2)0.091 (2)0.0340 (19)0.0387 (18)0.0478 (18)
C460.127 (3)0.143 (3)0.094 (2)0.058 (3)0.057 (2)0.069 (2)
Geometric parameters (Å, º) top
F1—C41.364 (4)C21—H21B0.9700
F2—C271.364 (5)C21—H21A0.9700
O1—C151.218 (3)C22A—H22B0.9700
O2—C381.220 (3)C22A—H22A0.9700
N1—C11.370 (3)C22B—H22D0.9700
N1—C141.378 (4)C22B—H22C0.9700
N2—C151.344 (4)C23A—H23A0.9600
N2—N31.384 (3)C23A—H23C0.9600
N3—C161.280 (5)C23A—H23B0.9600
N1—H1N0.85 (3)C23B—H23E0.9600
N2—H2N0.81 (3)C23B—H23D0.9700
N4—C371.378 (3)C23B—H23F0.9600
N4—C241.362 (4)C24—C291.405 (3)
N5—C381.349 (3)C24—C251.403 (5)
N5—N61.377 (4)C25—C261.367 (5)
N6—C391.280 (3)C26—C271.380 (5)
N4—H4N0.85 (3)C27—C281.368 (6)
N5—H5N0.77 (2)C28—C291.402 (5)
C1—C21.399 (5)C29—C301.433 (4)
C1—C61.407 (3)C30—C371.384 (3)
C2—C31.368 (5)C30—C311.488 (3)
C3—C41.394 (5)C31—C361.375 (5)
C4—C51.358 (5)C31—C321.385 (4)
C5—C61.400 (3)C32—C331.389 (4)
C6—C71.431 (4)C33—C341.362 (5)
C7—C141.383 (3)C34—C351.367 (4)
C7—C81.483 (3)C35—C361.382 (5)
C8—C131.386 (4)C37—C381.472 (4)
C8—C91.384 (4)C39—C401.497 (4)
C9—C101.374 (5)C39—C441.502 (4)
C10—C111.359 (5)C40—C411.509 (5)
C11—C121.377 (6)C41—C421.522 (6)
C12—C131.375 (5)C42—C431.518 (4)
C14—C151.475 (3)C42—C451.511 (5)
C16—C211.498 (5)C43—C441.515 (5)
C16—C171.489 (4)C45—C461.500 (5)
C17—C181.537 (6)C25—H250.9300
C18—C191.491 (6)C26—H260.9300
C19—C22A1.545 (8)C28—H280.9300
C19—C201.493 (6)C32—H320.9300
C19—C22B1.55 (2)C33—H330.9300
C20—C211.503 (6)C34—H340.9300
C22A—C23A1.472 (10)C35—H350.9300
C22B—C23B1.48 (3)C36—H360.9300
C2—H20.9300C40—H40A0.9700
C3—H30.9300C40—H40B0.9700
C5—H50.9300C41—H41A0.9700
C9—H90.9300C41—H41B0.9700
C10—H100.9300C42—H420.9800
C11—H110.9300C43—H43A0.9700
C12—H120.9300C43—H43B0.9700
C13—H130.9300C44—H44A0.9700
C17—H17B0.9700C44—H44B0.9700
C17—H17A0.9700C45—H45A0.9700
C18—H18A0.9700C45—H45B0.9700
C18—H18B0.9700C46—H46A0.9600
C19—H190.9800C46—H46B0.9600
C20—H20B0.9700C46—H46C0.9600
C20—H20A0.9700
C1—N1—C14109.5 (2)H22C—C22B—H22D107.00
N3—N2—C15120.6 (2)C23B—C22B—H22C108.00
N2—N3—C16116.5 (2)H23B—C23A—H23C110.00
C14—N1—H1N125.6 (18)C22A—C23A—H23B109.00
C1—N1—H1N123.8 (18)H23A—C23A—H23B109.00
N3—N2—H2N128 (2)H23A—C23A—H23C109.00
C15—N2—H2N112 (2)C22A—C23A—H23C110.00
C24—N4—C37109.2 (2)C22A—C23A—H23A109.00
N6—N5—C38121.6 (2)C22B—C23B—H23F110.00
N5—N6—C39116.6 (2)C22B—C23B—H23E110.00
C37—N4—H4N120 (2)H23D—C23B—H23F109.00
C24—N4—H4N129.1 (19)H23E—C23B—H23F110.00
C38—N5—H5N110.6 (19)H23D—C23B—H23E109.00
N6—N5—H5N127.1 (19)C22B—C23B—H23D109.00
N1—C1—C6107.5 (2)N4—C24—C25130.3 (2)
N1—C1—C2130.8 (2)N4—C24—C29108.2 (2)
C2—C1—C6121.7 (2)C25—C24—C29121.6 (3)
C1—C2—C3117.8 (3)C24—C25—C26117.5 (3)
C2—C3—C4119.8 (3)C25—C26—C27120.5 (4)
F1—C4—C3117.4 (3)F2—C27—C28118.8 (3)
C3—C4—C5123.9 (3)C26—C27—C28123.9 (4)
F1—C4—C5118.7 (3)F2—C27—C26117.3 (4)
C4—C5—C6117.2 (2)C27—C28—C29116.7 (3)
C1—C6—C5119.5 (2)C28—C29—C30133.1 (2)
C5—C6—C7132.9 (2)C24—C29—C28119.8 (3)
C1—C6—C7107.6 (2)C24—C29—C30107.1 (2)
C8—C7—C14129.5 (2)C31—C30—C37127.6 (2)
C6—C7—C14106.3 (2)C29—C30—C37106.3 (2)
C6—C7—C8124.2 (2)C29—C30—C31126.1 (2)
C7—C8—C9121.4 (2)C30—C31—C36123.0 (2)
C7—C8—C13120.6 (3)C32—C31—C36117.6 (3)
C9—C8—C13117.9 (3)C30—C31—C32119.4 (2)
C8—C9—C10121.4 (3)C31—C32—C33121.0 (3)
C9—C10—C11119.9 (4)C32—C33—C34120.1 (3)
C10—C11—C12119.9 (3)C33—C34—C35119.7 (3)
C11—C12—C13120.4 (4)C34—C35—C36120.3 (3)
C8—C13—C12120.4 (4)C31—C36—C35121.3 (3)
N1—C14—C15117.9 (2)N4—C37—C30109.3 (2)
N1—C14—C7109.2 (2)N4—C37—C38117.9 (2)
C7—C14—C15132.8 (2)C30—C37—C38132.8 (2)
O1—C15—C14121.7 (2)N5—C38—C37115.6 (2)
N2—C15—C14114.3 (2)O2—C38—N5122.5 (3)
O1—C15—N2124.0 (2)O2—C38—C37122.0 (2)
N3—C16—C17128.9 (3)N6—C39—C44116.5 (2)
C17—C16—C21114.7 (3)C40—C39—C44115.4 (2)
N3—C16—C21116.4 (3)N6—C39—C40128.1 (3)
C16—C17—C18110.0 (3)C39—C40—C41113.3 (3)
C17—C18—C19116.1 (3)C40—C41—C42113.4 (3)
C18—C19—C22A117.0 (4)C41—C42—C43108.8 (3)
C18—C19—C22B95.2 (8)C41—C42—C45113.4 (3)
C18—C19—C20111.0 (4)C43—C42—C45113.1 (3)
C20—C19—C22A108.7 (4)C42—C43—C44110.8 (3)
C20—C19—C22B144.0 (10)C39—C44—C43112.3 (3)
C19—C20—C21113.2 (4)C42—C45—C46114.0 (3)
C16—C21—C20111.3 (3)C24—C25—H25121.00
C19—C22A—C23A114.0 (6)C26—C25—H25121.00
C19—C22B—C23B117.7 (17)C25—C26—H26120.00
C1—C2—H2121.00C27—C26—H26120.00
C3—C2—H2121.00C27—C28—H28122.00
C2—C3—H3120.00C29—C28—H28122.00
C4—C3—H3120.00C31—C32—H32119.00
C6—C5—H5121.00C33—C32—H32119.00
C4—C5—H5121.00C32—C33—H33120.00
C10—C9—H9119.00C34—C33—H33120.00
C8—C9—H9119.00C33—C34—H34120.00
C9—C10—H10120.00C35—C34—H34120.00
C11—C10—H10120.00C34—C35—H35120.00
C10—C11—H11120.00C36—C35—H35120.00
C12—C11—H11120.00C31—C36—H36119.00
C13—C12—H12120.00C35—C36—H36119.00
C11—C12—H12120.00C39—C40—H40A109.00
C12—C13—H13120.00C39—C40—H40B109.00
C8—C13—H13120.00C41—C40—H40A109.00
C18—C17—H17B110.00C41—C40—H40B109.00
C16—C17—H17A110.00H40A—C40—H40B108.00
C16—C17—H17B110.00C40—C41—H41A109.00
C18—C17—H17A110.00C40—C41—H41B109.00
H17A—C17—H17B108.00C42—C41—H41A109.00
C17—C18—H18A108.00C42—C41—H41B109.00
C17—C18—H18B108.00H41A—C41—H41B108.00
C19—C18—H18A108.00C41—C42—H42107.00
C19—C18—H18B108.00C43—C42—H42107.00
H18A—C18—H18B107.00C45—C42—H42107.00
C18—C19—H19106.00C42—C43—H43A110.00
C22B—C19—H1988.00C42—C43—H43B110.00
C20—C19—H19107.00C44—C43—H43A109.00
C22A—C19—H19107.00C44—C43—H43B109.00
H20A—C20—H20B108.00H43A—C43—H43B108.00
C19—C20—H20A109.00C39—C44—H44A109.00
C21—C20—H20B109.00C39—C44—H44B109.00
C19—C20—H20B109.00C43—C44—H44A109.00
C21—C20—H20A109.00C43—C44—H44B109.00
H21A—C21—H21B108.00H44A—C44—H44B108.00
C16—C21—H21B109.00C42—C45—H45A109.00
C20—C21—H21A109.00C42—C45—H45B109.00
C20—C21—H21B109.00C46—C45—H45A109.00
C16—C21—H21A109.00C46—C45—H45B109.00
C19—C22A—H22A109.00H45A—C45—H45B108.00
C19—C22A—H22B109.00C45—C46—H46A109.00
H22A—C22A—H22B108.00C45—C46—H46B109.00
C23A—C22A—H22B109.00C45—C46—H46C109.00
C23A—C22A—H22A109.00H46A—C46—H46B109.00
C19—C22B—H22C108.00H46A—C46—H46C110.00
C19—C22B—H22D108.00H46B—C46—H46C110.00
C23B—C22B—H22D108.00
C1—N1—C14—C15176.4 (2)N3—C16—C21—C20126.5 (4)
C14—N1—C1—C2179.8 (3)C16—C17—C18—C1947.8 (5)
C14—N1—C1—C60.9 (3)C17—C18—C19—C22A175.1 (4)
C1—N1—C14—C71.3 (3)C17—C18—C19—C2049.5 (6)
C15—N2—N3—C16175.1 (3)C22A—C19—C20—C21178.0 (4)
N3—N2—C15—O12.9 (4)C18—C19—C20—C2151.9 (5)
N3—N2—C15—C14175.6 (2)C18—C19—C22A—C23A65.3 (7)
N2—N3—C16—C21177.0 (3)C20—C19—C22A—C23A168.0 (5)
N2—N3—C16—C173.0 (5)C19—C20—C21—C1654.1 (5)
C37—N4—C24—C291.0 (3)C25—C24—C29—C30178.4 (3)
C24—N4—C37—C38178.8 (2)N4—C24—C25—C26179.1 (3)
C37—N4—C24—C25178.4 (3)C29—C24—C25—C261.5 (5)
C24—N4—C37—C300.6 (3)N4—C24—C29—C301.1 (3)
C38—N5—N6—C39175.5 (3)C25—C24—C29—C281.7 (4)
N6—N5—C38—O26.1 (4)N4—C24—C29—C28178.8 (3)
N6—N5—C38—C37174.1 (2)C24—C25—C26—C270.7 (5)
N5—N6—C39—C44178.9 (2)C25—C26—C27—F2178.8 (3)
N5—N6—C39—C403.8 (4)C25—C26—C27—C280.1 (6)
N1—C1—C2—C3179.6 (3)C26—C27—C28—C290.3 (6)
N1—C1—C6—C70.2 (3)F2—C27—C28—C29179.0 (3)
C6—C1—C2—C31.2 (5)C27—C28—C29—C30179.1 (3)
C2—C1—C6—C51.1 (4)C27—C28—C29—C241.0 (4)
N1—C1—C6—C5179.6 (2)C28—C29—C30—C313.0 (5)
C2—C1—C6—C7179.6 (3)C24—C29—C30—C370.8 (3)
C1—C2—C3—C40.2 (5)C28—C29—C30—C37179.1 (3)
C2—C3—C4—F1177.5 (3)C24—C29—C30—C31177.1 (2)
C2—C3—C4—C51.9 (6)C29—C30—C37—N40.1 (3)
C3—C4—C5—C62.0 (5)C29—C30—C31—C3277.2 (4)
F1—C4—C5—C6177.4 (3)C29—C30—C37—C38177.7 (3)
C4—C5—C6—C10.5 (4)C31—C30—C37—N4177.7 (2)
C4—C5—C6—C7178.6 (3)C37—C30—C31—C3676.8 (4)
C5—C6—C7—C14178.7 (3)C37—C30—C31—C32100.2 (3)
C5—C6—C7—C82.9 (5)C31—C30—C37—C384.5 (4)
C1—C6—C7—C140.5 (3)C29—C30—C31—C36105.7 (3)
C1—C6—C7—C8177.9 (2)C32—C31—C36—C352.3 (5)
C8—C7—C14—N1177.3 (3)C30—C31—C36—C35174.9 (3)
C6—C7—C8—C978.4 (3)C30—C31—C32—C33174.1 (3)
C6—C7—C14—N11.1 (3)C36—C31—C32—C333.1 (5)
C14—C7—C8—C1379.2 (4)C31—C32—C33—C341.8 (6)
C6—C7—C14—C15176.2 (3)C32—C33—C34—C350.6 (6)
C6—C7—C8—C1398.9 (3)C33—C34—C35—C361.5 (6)
C14—C7—C8—C9103.5 (4)C34—C35—C36—C310.0 (6)
C8—C7—C14—C155.5 (5)N4—C37—C38—N5164.4 (2)
C13—C8—C9—C100.5 (4)C30—C37—C38—O2162.2 (3)
C9—C8—C13—C120.8 (4)C30—C37—C38—N517.9 (4)
C7—C8—C13—C12176.6 (3)N4—C37—C38—O215.5 (4)
C7—C8—C9—C10176.8 (3)N6—C39—C40—C41139.8 (3)
C8—C9—C10—C110.1 (5)C44—C39—C40—C4142.9 (4)
C9—C10—C11—C120.4 (5)N6—C39—C44—C43135.5 (3)
C10—C11—C12—C130.1 (5)C40—C39—C44—C4346.9 (4)
C11—C12—C13—C80.6 (5)C39—C40—C41—C4248.0 (4)
C7—C14—C15—O1168.5 (3)C40—C41—C42—C4356.4 (4)
C7—C14—C15—N213.1 (4)C40—C41—C42—C45176.8 (3)
N1—C14—C15—N2164.0 (2)C41—C42—C43—C4459.6 (4)
N1—C14—C15—O114.5 (4)C45—C42—C43—C44173.4 (3)
C21—C16—C17—C1849.2 (4)C41—C42—C45—C4672.2 (4)
N3—C16—C17—C18130.9 (4)C43—C42—C45—C46163.3 (4)
C17—C16—C21—C2053.6 (5)C42—C43—C44—C3955.4 (4)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg3, Cg5 and Cg7 are the centroids of the N1/C1/C6/C7/C14, C8–C13, N4/C24/C29/C30/C37 and C31–C36 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.85 (3)2.00 (3)2.836 (3)168 (3)
N4—H4N···O10.85 (3)2.08 (3)2.887 (3)160 (2)
C17—H17A···N20.972.462.834 (5)102
C40—H40A···N50.972.452.822 (4)102
C9—H9···Cg1i0.932.813.636 (3)149
C17—H17A···Cg30.972.873.820 (3)165
C40—H40A···Cg70.972.793.727 (4)163
C40—H40B···Cg5ii0.972.653.595 (4)163
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg3, Cg5 and Cg7 are the centroids of the N1/C1/C6/C7/C14, C8–C13, N4/C24/C29/C30/C37 and C31–C36 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.85 (3)2.00 (3)2.836 (3)168 (3)
N4—H4N···O10.85 (3)2.08 (3)2.887 (3)160 (2)
C9—H9···Cg1i0.932.813.636 (3)149
C17—H17A···Cg30.972.873.820 (3)165
C40—H40A···Cg70.972.793.727 (4)163
C40—H40B···Cg5ii0.972.653.595 (4)163
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+2.
 

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). This work was supported by the Scientific Research Projects Coordination Unit of İstanbul University (project No. T-471/25062004).

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